Naphthalanmorpholin.



UNITED STATES PATENT OFFICE.

LUDWIG KNORR, OF JENA, GERMANY, ASSIGNOR TO THE FARBWERKE, VORMALSMEISTER, LUOIUS & BRUNING, OF I-I6GI-IST-ON-THE-MAIN,

GERMANY.

NAPHTHALANMORPHOLIN.

SPECIFICATION forming part of Letters Patent No. 641,870, dated January23, 1900.

Application filed February 4, 1899.

(R representing a monovalent alcoholic radical,) with acids, newcompounds may be obtained, which are to be called naphthalanmorpholins,having the constitution of o on, o H

N(alky1) 0H,.

These new compounds are valuable, as they possess the action of morphin,and may thus be employed as its substitute.

I illustrate my process by the following example: One hundred andforty-six parts,

by weight, of dihydronaphthalene oxid and T ninety parts, by weight, ofethylethanolamin are heated for some hours to to centigrade, when theethylethanol-amidotetrahydronaphthol thus obtained is separated from theproduct of reaction by means of alkali. An isolation, however, isunnecessary, and in order to transform it into the correspondingethylnaphthalanmorpholin the product of reaction is heated directly withfive to ten times the quantity of sulfuric acid of sixty to seventy percent. strength to 140 to centigrade. The acid solution is then dilutedwith water and the naphthalene thus formed and the unchangeddihydronaphthalene oxid Serial No. 704,452. (Specimens) removed bydistillation with water. Then a1 kali is added and the morpholin isdissolved by shaking with ether. Ethylnaphthalanmor pholin is an oildistilling at 320 centigrade; its chlorhydrate crystallizes in prismsfrom alcohol; its aqueous solution reacts in a neutral manner, and itmelts at 237 to 238 centigrade. The base is easily soluble in alcohol,ether, and benzene, and soluble with difficulty in water.

In a corresponding manner analogously-constituted basessuch asnaphthalanmorpho lin, methylnaphthalanmorpholin, and ethanolnaphthalanmorpholin-may be obtained in employing ethanolamin,methylethanolamin, and diethanolamin instead of ethylethanolamin.

Having now described my invention, what I claim is 1. As new productsthe naphthalanmorpho lins of the general formula:

o -oH,

being basic compounds which combine with acids to crystalline saltssoluble in water with a neutral reaction, colorless and easily solublein alcohol, ether, benzene and soluble with difficulty in water.

2. As a new product the ethylnaphthalanmorpholin, being a thick oil,distilling at 320 centigrade, forming a chlorhydrate crystallizing inprisms, melting at 237 to 238 centigrade, soluble in water with aneutral reaction, the oil is easily soluble in alcohol, ether, benzeneand soluble with difficulty in water.

In testimony that I claim the foregoing as my invention 1 have signed myname in presence of two subscribing witnesses.

LUDWIG KNORR.

Witnesses:

ELISABETH KNORR, T. E. MOORE.

